And while Howard Stern may be one of the most successful shock jocks in history, a bulk of his estimated net worth of $600 million comes from so much more than radio. He’s the author of the highly popular books “Private Parts” and “Miss America.” He was also the host of “America’s Got Talent” until 2015, which made him roughly $15 million per year.

But the bulk of his entertainment value comes from his radio program. Take a look back at some of his wackiest, most outrageous and most hilarious moments through the years.

When he chatted with Bill O’Reilly about his career in show business:

When he chatted with Conan O’Brien about pranking Bill Cosby:

When he got his guest, Gilbert Gottfried, to do a nearly 10-minute impression of Jerry Seinfeld:

When he found out his producer, Gary, made a message for his girlfriend (who’d just broken up with him) to take him back, and he aired it on live radio:

When he got Gwen Stefani to explain what the heck a “Hollaback Girl” is:

When he got Madonna to discuss what dating Tupac was like:

When one of his long-time side kicks, Artie quit live on air:

And most recently, when he had Lindsay Lohan discuss her rise, fall, and rise again:

No doubt Howard Stern is one of the most outlandish hosts on air today. And it doesn’t look like he’s going to slow down anytime soon.